16 days in Oregon Itinerary

16 days in Oregon Itinerary

Created using Inspirock Oregon trip planner

Plan created by another user. Make it yours
1
Medford
— 1 night
2
Crater Lake National Park
— 1 night
3
Bend
— 3 nights
4
Hood River
— 2 nights
5
Cannon Beach
— 2 nights
6
Portland
— 6 nights

S M T W T F S
27
28
29
30
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17

1
night
Medford

Medford ©
Medford is a city in, and county seat of, Jackson County, Oregon, United States. Kick off your visit on the 30th (Wed): explore the activities along Rogue River and then catch a live performance at Oregon Shakespeare Festival. Get ready for a full day of sightseeing on the next day: tour the pleasant surroundings at Natural Bridge Loop, whizz through the canopy at Rogue Valley ZipLine Adventure, and then examine the collection at Bear Hotel Artworks Museum.

To see more things to do, reviews, other places to visit, and other tourist information, read Medford trip builder.

Charlotte to Medford is an approximately 9.5-hour flight. You can also drive. You'll gain 3 hours traveling from Charlotte to Medford due to the time zone difference. Traveling from Charlotte in September, Medford is a bit cooler at night with lows of 53°F. Wrap up your sightseeing on the 1st (Thu) to allow time to drive to Crater Lake National Park.

Things to do in Medford

Outdoors · Adventure · Parks

Side Trips

Rogue Valley ZipLine Adventure, Oregon Shakespeare Festival, Bear Hotel Artworks Museum
Highlights from your plan
Rogue Valley ZipLine Adventure ©
Rogue Valley ZipLine Adventure
Rogue River ©
Rogue River
Oregon Shakespeare Festival ©
Oregon Shakespeare Festival

1
night
Crater Lake National Park

Crater Lake National Park ©
Reaching a depth of 592 m (1,943 ft), Crater Lake is the deepest lake in the United States.
Kick off your visit on the 2nd (Fri): explore the striking landscape of Crater Lake National Park.

For more things to do, maps, traveler tips, and more tourist information, use the Crater Lake National Park trip planner.

You can drive from Medford to Crater Lake National Park in 2 hours. Expect a daytime high around 71°F in October, and nighttime lows around 44°F. Wrap up your sightseeing on the 2nd (Fri) early enough to drive to Bend.

Things to do in Crater Lake National Park

Nature · Parks
Highlights from your plan
Crater Lake National Park ©
Crater Lake National Park

3
nights
Bend

Bend ©
An old logging town at the crux of the high desert and ponderosa pine forest, Bend melds a love of the outdoors with cosmopolitan flair.
Explore the numerous day-trip ideas around Bend: Smith Rock State Park (in Redmond) and Dee Wright Observatory (in Blue River). There's lots more to do: see the interesting displays at High Desert Museum, head outdoors with RiverStone Adventures, walk around Drake Park, and explore the wealth of natural beauty at Deschutes National Forest.

To see where to stay, ratings, photos, and more tourist information, refer to the Bend trip itinerary builder.

You can drive from Crater Lake National Park to Bend in 3 hours. Alternatively, you can do a combination of taxi and bus. Prepare for little chillier weather when traveling from Crater Lake National Park in October: high temperatures in Bend hover around 62°F and lows are around 37°F. Cap off your sightseeing on the 5th (Mon) early enough to go by car to Hood River.

Things to do in Bend

Parks · Nature · Outdoors

Side Trips

Smith Rock State Park, Dee Wright Observatory
Highlights from your plan
Smith Rock State Park ©
Smith Rock State Park
High Desert Museum ©
High Desert Museum
Deschutes National  Forest
Deschutes National Forest

2
nights
Hood River

Hood River ©
The city of Hood River is the seat of Hood River County, Oregon, United States. Kick off your visit on the 6th (Tue): contemplate the waterfront views at Columbia River Gorge National Scenic Area, then see the interesting displays at Columbia Gorge Discovery Center & Museum, and then see the interesting displays at Fire Museum in City Hall. Get ready for a full day of sightseeing on the next day: stroll through Historic Columbia River Highway State Trail, cruise along Hood River County Fruit Loop, and then examine the collection at Western Antique Aeroplane & Automobile Museum.

To find reviews, ratings, other places to visit, and tourist information, you can read our Hood River road trip planning app.

Getting from Bend to Hood River by car takes about 3.5 hours. Other options: fly; or take a bus. Plan for a bit warmer nights when traveling from Bend in October since evenings lows in Hood River dip to 45°F. Finish up your sightseeing early on the 7th (Wed) so you can go by car to Cannon Beach.

Things to do in Hood River

Parks · Museums · Nature

Side Trips

Oregon, The Dalles, Historic Columbia River Highway State Trail
Highlights from your plan
Columbia River Gorge National Scenic Area ©
Columbia Gorge Discovery Center & Museum ©

2
nights
Cannon Beach

Cannon Beach ©
Cannon Beach is a city in Clatsop County, Oregon, United States. Kick off your visit on the 8th (Thu): enjoy the sand and surf at Cannon Beach, take in the exciting artwork at Icefire Glassworks, then explore the striking landscape at Haystack Rock, and finally admire the majestic nature at Hug Point State Park. On the 9th (Fri), you'll have a packed day of sightseeing: kick back and relax at Manzanita Beach, stroll through Cedar Wetlands Preserve, then immerse yourself in nature at Oswald West State Park, and finally immerse yourself in nature at Ecola State Park.

To see ratings, photos, more things to do, and other tourist information, read our Cannon Beach trip planner.

You can drive from Hood River to Cannon Beach in 3 hours. Alternatively, you can take a bus; or do a combination of train and bus. In October, daytime highs in Cannon Beach are 63°F, while nighttime lows are 48°F. Wrap up your sightseeing on the 9th (Fri) to allow time to drive to Portland.

Things to do in Cannon Beach

Parks · Nature · Outdoors

Side Trips

Manzanita Beach, Cedar Wetlands Preserve
Highlights from your plan
Haystack Rock ©
Haystack Rock
Cannon Beach ©
Cannon Beach
Ecola State Park ©
Ecola State Park

6
nights
Portland

Portland ©
A big city with a small-town feel, Portland is home to the country's biggest rose test garden, perched on a hill overlooking downtown.
Get out of town with these interesting Portland side-trips: Evergreen Aviation & Space Museum (in McMinnville), Bravuro Cellars (in Newberg) and Pumpkin Ridge Zip Tour (in North Plains). Dedicate the 12th (Mon) to wine at some of the top wineries in the area. There's lots more to do: admire the natural beauty at Portland Japanese Garden, contemplate the long history of Columbia River Highway, look for gifts at Powell's City of Books, and admire the striking features of Pittock Mansion.

For maps, more things to do, where to stay, and more tourist information, read our Portland travel route builder.

Drive from Cannon Beach to Portland in 1.5 hours. Alternatively, you can take a bus. In October, daytime highs in Portland are 66°F, while nighttime lows are 49°F. Wrap up your sightseeing by early afternoon on the 15th (Thu) to allow enough time to travel back home.

Things to do in Portland

Tours · Wineries · Parks

Side Trips

Troutdale, Evergreen Aviation & Space Museum, Bravuro Cellars, Pumpkin Ridge Zip Tour, Multnomah Falls
Highlights from your plan
Portland Japanese Garden ©
Portland Japanese Garden
International Rose Test Garden ©
International Rose Test Garden
Powell's City of Books ©
Powell's City of Books

Similar plans

18 days in United States BY A USER FROM UNITED STATES August, culture, outdoors, relaxing, beaches, museums, shopping, wildlife, popular & hidden gems Preferences: August, culture, outdoors, relaxing, beaches, museums, shopping, wildlife Attraction style: Popular & hidden gems Pace: Medium 30 days in Oregon & Washington State BY A USER FROM UNITED STATES September, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, wildlife, popular & hidden gems Preferences: September, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, wildlife Attraction style: Popular & hidden gems Pace: Medium 17 days in United States BY A USER FROM UNITED STATES September, outdoors, relaxing, beaches, historic sites, museums, wildlife, hidden gems Preferences: September, outdoors, relaxing, beaches, historic sites, museums, wildlife Attraction style: Hidden gems Pace: Medium 36 days in United States BY A USER FROM UNITED STATES August, outdoors, relaxing, romantic, beaches, shopping, wildlife, popular & hidden gems Preferences: August, outdoors, relaxing, romantic, beaches, shopping, wildlife Attraction style: Popular & hidden gems Pace: Medium 36 days in United States BY A USER FROM GUERNSEY September, culture, outdoors, relaxing, romantic, beaches, historic sites, wildlife, popular & hidden gems Preferences: September, culture, outdoors, relaxing, romantic, beaches, historic sites, wildlife Attraction style: Popular & hidden gems Pace: Medium 21 days in United States BY A USER FROM UNITED STATES June, teens, culture, outdoors, beaches, historic sites, museums, wildlife, popular & hidden gems Preferences: June, teens, culture, outdoors, beaches, historic sites, museums, wildlife Attraction style: Popular & hidden gems Pace: Medium 25 days in United States BY A USER FROM UNITED STATES November, teens, kids, outdoors, relaxing, beaches, historic sites, wildlife, popular & hidden gems Preferences: November, teens, kids, outdoors, relaxing, beaches, historic sites, wildlife Attraction style: Popular & hidden gems Pace: Medium 24 days in United States BY A USER FROM UNITED STATES September, culture, outdoors, relaxing, beaches, historic sites, wildlife, popular & hidden gems Preferences: September, culture, outdoors, relaxing, beaches, historic sites, wildlife Attraction style: Popular & hidden gems Pace: Medium 27 days in Oregon & Houston BY A USER FROM UNITED STATES August, teens, culture, outdoors, relaxing, fast-paced, hidden gems Preferences: August, teens, culture, outdoors, relaxing Attraction style: Hidden gems Pace: Fast-paced 11 days in Oregon BY A USER FROM UNITED STATES September, culture, outdoors, relaxing, romantic, beaches, historic sites, wildlife, popular & hidden gems Preferences: September, culture, outdoors, relaxing, romantic, beaches, historic sites, wildlife Attraction style: Popular & hidden gems Pace: Medium 9 days in Oregon BY A USER FROM UNITED STATES July, culture, outdoors, relaxing, beaches, historic sites, wildlife, slow & easy, popular & hidden gems Preferences: July, culture, outdoors, relaxing, beaches, historic sites, wildlife Attraction style: Popular & hidden gems Pace: Slow & easy 14 days in Oregon BY A USER FROM UNITED STATES June, kids, outdoors, historic sites, popular & hidden gems Preferences: June, kids, outdoors, historic sites Attraction style: Popular & hidden gems Pace: Medium
See more plans